Methyl iodide → HCID 14692991, compound

HRID 1031859Notes

Reaction equation

HRID 1031859 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:18])[CH:9]=[C:8]([CH3:10])[CH2:7][C:6]([CH3:12])([CH3:11])[CH:5]1[C:13](=[CH2:17])[CH2:14][CH2:15][OH:16].[CH3:19]I>CCCCCC.C1COCC1>[CH3:19][O:16][CH2:15][CH2:14][C:13](=[CH2:17])[CH:5]1[C:6]([CH3:11])([CH3:12])[CH2:7][C:8]([CH3:10])=[CH:9][C:4]1([CH3:18])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14692978HCID 14692978, compound

Product 1

HCID 14692991HCID 14692991, compoundYield 465.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Sodium hydride (0.6g of 60% oil dispersion, 0.015 mol) was washed with hexane (2×3 mL) and suspended in THF (10 mL). A solution of 2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol (1.11g, 0.005 mol) in THF (5 mL) was added, followed by methyl iodide (1.4g, 0.001 mol). The mixture was heated at reflux for 4 hr. Afterwhich, work-up, chromatography and kugelrohr distillation gave 1.10g of 2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol methyl ether. 1H-NMR (60 MHz, CDCl3) δ0.95 (6H, s), 1.03 (6H, broad s), 1.63 (3H, broad s), 1.5-2.6 (5H, m), 3.33 (3H, s) 3.58 (2H, t, J =7 Hz), 4.85-5.15 (3H, m); IR (film) vmax 2960, 1640, 1440, 1380, 1360 cm-1 ; MS m/e 236, 221, 204, 189, 140, 125, 96.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hr
  3. distillationchromatography and kugelrohr distillation

Sources & evidence

ORD record
ord-7c71ddd710da45829fe23d9dc4d8d1d7
Source dataset
uspto-grants-1990_09
Patent number
US04956342

Reaction notes

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